Overview
Lately, I've been thinking a lot about assassins in D&D 5e ever since I introduced an assassin's guild into my Tri-Panthonic War Campaign. That definitely includes the subclass for Rogues in the Player's Handbook, but it's not limited to that.
I thought to myself: "What's the best way to create an assassin? What's the best way to create a character that has the ability to kill someone in the dead of night, potentially impersonate them, and never be found?" An Assassin Rogue would seem like the best avenue, right? Well, I think that that particular class / subclass combination is only part of it.
What happens if we multiclass? Is there, in fact, a better way to build an assassin in D&D 5e? Obviously, this is all based in my opinion and (as I tend to do for these concept ideas) there will be several options available for preferred play styles and aesthetics. So, let's explore this idea!
Race, Class, Stats, and Background
Let's start with class, since that's probably the easiest and the thing that's the most "set in stone" already. Assassin Rogue is almost definitely at least one of the classes that you want in this build. This is idea is based around the aesthetic of "assassin" which, in my mind, means:
- Having the ability to kill people quickly - Sneak Attack and Assassinate.
- Hide and run away quickly - Rogues can get some serious Stealth modifiers and can hide, disengage, or dash as a bonus action.
- Potentially being able to impersonate people, or certain types of people - Assassins have a 9th level feature to do this, but that takes in-game time and money.
I have a couple of classes in mind to multiclass into that would make our lives as an assassin a little easier.
Gloom Stalker Rangers (Xanathar's Guide) are a great place to start. Dexterity and Wisdom are going to be your highest stats for this version. If I were playing this and the Assassin Rogue, I'd personally take more levels in this class than in Rogue and here's why. Gloom Stalkers, at Level 3, are invisible in darkness even to creatures who rely on darkvision. Also at Level 3, they gain a boost to their initiative equal to their Wisdom modifier. Imagine being able to max out Wisdom and Dexterity, and then taking the Alert feat. You'd have a +15 to your initiative; you'd pretty much always go first and you'd always get that sweet Assassinate feature. Then, if you hit, you get the sneak attack damage.
If I was going in that direction, I'd shoot to be a Level 20 character with 13 levels in Gloom Stalker and 7 levels in Assassin.
- You go through Rogue long enough to have 4d6 sneak attack damage and you still get the Evasion feature which, in my opinion, is one of the best features in the game. The sneak damage isn't as high as it could be, but it's still sizeable enough, even at high levels.
- You don't get the Assassin's Level 9 Infiltration Expertise feature, but you do get the Disguise Self spell from Gloom Stalker at Level 3.
- You get the Fear spell at Level 9, which is great if you want people to fear you or to suddenly run away from you instead of towards you.
- Gloom Stalkers also have an 11th level ability that allows them to make an additional attack if they miss their first attack, once on each turn.
If you prefer the spellcaster route, but still want that assassin flare, I can think of two other classes and subclasses that could pair really well with an Assassin Rogue.
The first is the College of Whispers Bard. (Xanathar's Guide) They have the "fear me" factor via their Level 3 Words of Terror feature and they also have the ability to impersonate the dead. Say your party killed someone who was mid-rank in a cult. You could use the Level 6 ability, Mantle of Whispers, and become that person for an hour to infiltrate and spy. You gain basic information about them when you do this so you can successfully pass yourself off. You could do a triple multiclass with this and the Gloom Stalker to have some real fear on your side. Imagine an Assassin Rogue 7 / Whispers Bard 6 / Gloom Stalker 7 as a Level 20 character. That's scary.
Another option for a spellcasting multiclass is the Shadow Magic Sorcerer. (Xanathar's Guide) Personally, I'm not a huge fan of this multiclass because although it has some excellent teleportation abilities, those abilities don't come into play until Level 14. So you could multiclass and do Assassin Rogue 6 / Shadow Sorcerer 14 but then you miss out on the Rogue's Evasion feature, which would actually serve you very well in this case because you'd certainly be a glass cannon type. The only good thing is that you'd get access to some really good disguise, illusion, and fear-inducing spells for infiltration and getaway. There's more utility and adaptability here.
For both of those options, you're going to want to make sure you have high Charisma too, for spellcasting.
Background isn't so important with this build. Criminal (Player's Handbook) is always a good option if you're killing illegally or as part of some gang or other shady group. The backgrounds Urban Bounty Hunter and Mercenary Veteran (both from Sword Coast Adventurer's Guide) are also applicable to this build.
Race also isn't all that important, but I do have my own personal preference. This build has a lot to do with darkness and a lot of abilities that play into being good in the dark. I'd go with Drow, or Dark Elf (Player's Handbook) because they receive the elven +2 to Dexterity and they get 120 feet of darkvision. Add that to the Gloom Stalker feature, Umbral Sight, and you can get 150 feet of darkvision if you choose that class option.
Roleplay Potential
You could be the scariest person in your adventuring party by using this build, if you really wanted to. This character is good at getting into places and out of places undetected and unnoticed. They can deal some serious damage and, with the initiative bonus they get, they are usually faster than their enemies.
Depending on what you decide you want your backstory to be, that can also play into the campaign in multiple different ways. Say you worked for an assassin's guild before adventuring. Well, that same guild is plotting to kill the king now, and you and your adventuring party have been working for the king this whole time. Maybe the gang you were in is upset that you left, and actively hunting you down.
An assassin doesn't only have had to be an assassin either. Perhaps, they're actually quite good at something else or other things. They could have a family; I love it when characters have families in D&D. Killing is just what they do for a living because it pays well, regardless of whether it was wrong or right. Depending on the alignments (or general morals, for all those folks that don't play with alignment) of the rest of your party, you might get along great with them. The Lawful Good people in your party might not approve of your approach, but in the end... does it matter if you get the job done? There's room for growth there on all sides.
Assassins come in many forms, which is why I was so interested in seeing if we could take the features that are assassin-typical and fit other classes into them. I wanted to re-flavor the assassin in an effort to make an even better assassin. I hope I've succeeded with some of the ideas put forth here. I think these builds could be really fun to bring to your table.
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